Chicago in 7 Days — City + Detroit OR Indiana Dunes + NYC Extension

Activities

1. 07:30 Breakfast — Lou Mitchell's (since 1923, Route 66 starting point) 1 hour

   Legendary diner at 565 W Jackson — first stop on historic Route 66. Free Milk Duds + donut holes while you wait, oversized omelets, hash browns. $12-20 per person.

   Cost: $12-20 TIP: Open 5:30am weekdays / 7am weekends. Expect 20-40 min wait Sat/Sun. Cash-friendly tip jar.
2. 09:00 Cloud Gate ('The Bean') + Millennium Park 1.5 hours

   Anish Kapoor's mirrored bean sculpture — Chicago's signature photo. Reflect the skyline in distorted curves. Free, open year-round. Pair with Crown Fountain (1,000 video faces) and Pritzker Pavilion (Frank Gehry concert venue).

   Cost: Free TIP: Morning before 10am has no crowds. Sunset to blue hour for the gold-hour reflection.
3. 10:30 Art Institute of Chicago 2.5 hours

   Top US museum + 300,000 works. Hopper's Nighthawks, Wood's American Gothic, Seurat's Sunday on La Grande Jatte, Picasso, Monet. $32 entry.

   Cost: $32 TIP: CityPASS ($129 for 5 attractions) saves 40%. Modern Wing café for lunch break.
4. 13:00 Skip-line tip — Art Institute Modern Wing back entrance saves 15-30 min

   Most visitors queue at the Michigan Avenue main entrance (15-30 min summer). Walk to the Modern Wing entrance on Monroe Street — same ticket, no queue, opens into the Modern + Contemporary galleries with the Renzo Piano bridge connecting to Millennium Park.

   Cost: Same $32 TIP: Modern Wing entrance also has the better café (Terzo Piano, $20-35 lunch with Bean view).
5. 13:30 Lunch — Pizzeria Uno (since 1943, deep dish origin) 1.5 hours

   The original deep dish pizza, invented here. Order the Number 1 (Pizzeria Uno's classic). 45 min bake time + 30-60 min queue at peak.

   Cost: $20-30 TIP: Make reservation. One pizza feeds 2-3 people. Eat with knife + fork.
6. 14:30 Marina City + Wrigley Building architectural pause 20 min photo stop

   Marina City's twin corn-cob towers (1964, Bertrand Goldberg) along the Chicago River are unmissable from the State Street Bridge. Free outdoor photo. Wrigley Building (1921, white terracotta clock tower) sits across the river — also free to admire.

   Cost: Free TIP: Best photos at golden hour. The lower-level River Walk path passes both buildings for water-level shots.
7. 15:00 Magnificent Mile walk + Garrett Popcorn 2.5 hours

   Michigan Avenue 1.6 km luxury shopping: Tiffany, Apple flagship, Nordstrom. Stop at Garrett Popcorn (since 1949) for the iconic Chicago Mix.

   Cost: Shopping + $10-20 popcorn TIP: Garrett tin (decorative canister) is the souvenir-home format. November Light Festival is the Mag Mile's must-see event.
8. 16:30 Water Tower Place + Original Water Tower (1869, fire survivor) 30-45 min

   Free landmark — the limestone Water Tower at 806 N Michigan survived the 1871 Great Chicago Fire. Modern Water Tower Place mall (1976) houses American Girl Place flagship + 8 floors of retail. Free public restrooms + escape from weather.

   Cost: Free TIP: Water Tower itself houses City Gallery — free rotating photography exhibitions of Chicago history. American Girl Place is the must-stop if traveling with girls 6-12.
9. 17:30 360 Chicago Observation Deck (875 N Michigan, 94th floor, 314m) 1 hour

   Former John Hancock Center observation deck. Open-air Tilt feature pushes you outward 30 degrees over Michigan Avenue. Floor-to-ceiling lakefront panorama including Lincoln Park + Navy Pier. $30 standard.

   Cost: $30 (Tilt +$10) TIP: Sunset 19:00-20:30 (summer) for golden hour over the lake. Less queue than Willis Tower Skydeck. Pair with Signature Lounge on 96th floor for the no-entry-fee skyline cocktail at $18-22.
10. 18:30 Navy Pier (free entry + 60m Ferris Wheel) 1.5 hours

    1916 pleasure pier extending into Lake Michigan. Centennial Ferris Wheel $20, free entry. Summer fireworks Wed + Sat 21:30 (May-Sep) free.

    Cost: Free (Ferris Wheel $20) TIP: Summer fireworks are the highlight — arrive 21:00 for good spots. Otherwise sunset stroll on the pier is the visit.
11. 20:30 Dinner — Portillo's (Chicago hot dog + Italian beef) OR Cindy's Rooftop (Bean view sunset) 2 hours

    Portillo's $8-15 for the classic Chicago hot dog + Italian beef + chocolate cake shake combo. Cindy's Rooftop $35-80 for the sunset cocktail + Bean-view dinner.

    Cost: $8-80 TIP: Cindy's Rooftop requires booking 1+ week ahead for sunset window seats. Portillo's is the more casual heritage pick.

Meal Recommendations

Activities

1. 08:00 Breakfast — Wildberry Pancakes (Loop) OR Stan's Donuts (Wicker Park transit) 30-60 min

   Wildberry Pancakes (130 E Randolph) for stuffed pancakes $15-25, weekday no-line. Stan's Donuts (multiple locations) for the $4-6 Pocky donut or biscoff cake — quick takeaway pre-cruise.

   Cost: $5-25 TIP: Cruise dock is at Michigan Ave Bridge — Stan's Donuts on Lake St is a 10-min walk en route. Pick Wildberry only if you skipped Lou Mitchell's on Day 1.
2. 09:30 Chicago Architecture River Cruise (90 min, AIA #1 US tour) 2 hours

   Chicago Architecture Foundation 90-min cruise narrated by AIA-certified docents. 40+ buildings from 1880s pioneers to modern Aqua Tower (Jeanne Gang). The most-praised tour in Chicago.

   Cost: $52-60 TIP: Book 1+ week ahead — sells out summer. Upper open-deck seats for best photos (bring sunscreen + hat).
3. 12:00 Lunch — Lou Malnati's (locals' #1 deep dish) OR Al's Italian Beef (1938 original) 1.5 hours

   Lou Malnati's $20-30 with butter crust. Al's $6-10 for the original Italian beef sandwich (order 'wet').

   Cost: $6-30 TIP: Choose based on appetite: Italian beef is faster + cheaper; deep dish requires 45 min bake time.
4. 13:30 Chicago Cultural Center (free, 1897) 30-45 min

   78 E Washington — original Chicago Public Library building. Preston Bradley Hall has the world's largest Tiffany stained glass dome (38-foot diameter). Free entry, rotating art exhibitions, free Wi-Fi + restrooms. Underrated free stop between Loop attractions.

   Cost: Free TIP: Open 10am-5pm daily (12pm Sun). Free guided architecture tours Wed + Fri at 1:15pm. Perfect rainy-day backup or pre-Willis Tower stop.
5. 15:30 The Loop Public Art Walk (Picasso, Calder, Miró, Chagall) 45 min

   Free outdoor sculpture trail across Daley Plaza (Picasso untitled head, 1967) + Federal Plaza (Calder's red Flamingo, 1974) + Brunswick Plaza (Miró's Chicago, 1981) + Chase Plaza (Chagall's Four Seasons mosaic, 1974). 45 min walking loop, all free.

   Cost: Free TIP: Pick up the free 'Loop Public Art' map at Chicago Cultural Center information desk. Best afternoon light Picasso 2-4pm.
6. 14:00 Willis Tower Skydeck + The Ledge (442m, 103rd floor) 1.5 hours

   Formerly Sears Tower — world's tallest 1973-1998. The Ledge: 4 glass boxes extending 1.3m outside the building, glass floor at 412m. Views to 4 states on clear days.

   Cost: $39 standard / $45 Express TIP: Express +$6 worth it to skip 1-2 hour summer queue. Sunset 19:00-20:30 has the best photos.
7. 16:00 Chicago Riverwalk + Lakefront stroll 1.5 hours

   2 km waterfront walkway along Chicago River. Bridges, public art, café terraces. Sunset views of skyscrapers reflected in water.

   Cost: Free TIP: Best 1 hour before sunset. Pair with rooftop cocktail at LH Rooftop (LondonHouse) or City Winery for skyline views.
8. 17:30 Chinatown Square dim sum break (Cermak-Chinatown Red Line) 1 hour

   Chicago's Chinatown along Wentworth Avenue + Chinatown Square. MingHin Cuisine and Phoenix for cart-style dim sum, Joy Yee bubble tea, Chiu Quon Bakery (since 1986) for char siu bao. Quick $10-20 stop.

   Cost: $10-20 TIP: Red Line Cermak-Chinatown station drops you at Chinatown Gate. Dim sum carts run 10am-3pm — late afternoon catches the last rounds. Skip if not hungry — Greek Islands dinner is the headliner.
9. 18:30 Dinner — Greek Islands (Greek Town, since 1971, Saganaki) OR Smyth (2-Michelin West Loop) 2.5 hours

   Greek Islands $25-45 with the flaming Saganaki cheese ('Opa!' tableside). Smyth $300-400 for the 2-Michelin tasting menu (book 4-6 weeks ahead).

   Cost: $25-400 TIP: Smyth must be booked 4+ weeks ahead. Greek Islands accepts reservations.
10. 20:30 Optional Chicago Theatre marquee photo (Loop) 15 min photo stop

    175 N State — the 1921 Chicago Theatre marquee with the giant 'CHICAGO' lettering is the iconic Loop photo at night. Backlit, glows red. Free to photograph; tours $20 if interested.

    Cost: Free TIP: Walk 5 min from Andy's Jazz Club. Best photo angle from across State Street. Off-Loop Brown Line evening rides also pass it lit up.
11. 21:00 Live music — Buddy Guy's Legends (blues) OR Andy's Jazz Club (since 1951) 2 hours

    Buddy Guy's $15-50 cover + Cajun food. Andy's $15-35 cover + dinner. Both have nightly live music in River North-walking-distance venues.

    Cost: $15-50 TIP: Book 1 week ahead for weekends. January Buddy Guy residency requires 2+ months ahead.

Meal Recommendations

Activities

1. 08:30 Breakfast — Ann Sather (Lakeview, since 1945, cinnamon rolls) 1 hour

   909 W Belmont (Wrigleyville area). Swedish-American diner famous for fist-sized cinnamon rolls + lingonberry crepes. $12-18 per person. Drag Queen Bingo Brunch on some Sundays.

   Cost: $12-18 TIP: Open 7am-3pm. Cash + card. The cinnamon rolls are sold separately ($4) — order one extra to share. Walk distance to Wrigley.
2. 09:30 Boystown rainbow pylons walk (Lakeview LGBTQ+ district) 30 min

   North Halsted between Belmont + Grace was the first officially recognized LGBT neighborhood in the US (1997). 20 rainbow-striped pylons line the strip with plaques for LGBT history figures. Free walking landmark. Pride Parade end of June draws 1M+ visitors.

   Cost: Free TIP: Daytime walk feels safe + welcoming. Pride Weekend (last Sunday of June) is the city's biggest annual event after Lollapalooza. Sidetrack is the iconic karaoke bar if returning for nightlife.
3. 10:00 Wrigley Field (since 1914, Chicago Cubs) 3 hours

   Oldest MLB ballpark + Cubs game (Apr-Oct) $30-150 OR ballpark tour $25 (off-season). The ivy-covered outfield walls + manual scoreboard are unchanged since 1914.

   Cost: $25-150 TIP: Book 1+ week ahead for games. Off-season tour gives full ballpark access including press box + dugouts.
4. 13:30 Lunch — Portillo's (Chicago hot dog) OR Lou Malnati's (deep dish) 1 hour

   Pre-departure Chicago classic lunch. Portillo's $8-15 for hot dog + Italian beef. Lou Malnati's $20-30 for one last deep dish.

   Cost: $8-30 TIP: Wrigleyville has both within walking distance of the ballpark.
5. 14:30 Murphy's Bleachers + Wrigleyville bar crawl (post-game tradition) 1 hour

   Murphy's Bleachers (3655 N Sheffield) is the across-the-street Cubs fan bar since 1980. Pre-game or post-game beers $7-9 + Italian beef sandwiches $11. Cubs win = horn blasts and singing 'Go Cubs Go'. Skip if not a baseball fan.

   Cost: $15-25 TIP: Game days only — closed early on non-game off-season days. Slugger's, The Cubby Bear, and Sluggers across the intersection are alternatives.
6. 15:00 Lincoln Park Zoo (free, since 1868) 2 hours

   1.6 sq km lakefront park + 1868 zoo with free admission. Polar bears, gorillas, sea lions all free. Combined with Lincoln Park Conservatory (also free) and Nature Boardwalk.

   Cost: Free TIP: Best for families with kids. Cafe Brauer (1908 historic building) for snacks.
7. 15:30 Lincoln Park Conservatory + Alfred Caldwell Lily Pool (both free) 45 min

   Glass conservatory (1893) with 4 plant houses including 50-foot palm trees. The hidden gem next door is Alfred Caldwell Lily Pool — a Prairie-style designed water garden (1937), pure tranquility 200m from the zoo.

   Cost: Free TIP: Open 9am-5pm. Lily Pool is unmarked from the street — enter via the Fullerton + Stockton intersection. Photographer's hidden spot.
8. 16:00 North Avenue Beach + Lake Michigan shoreline (summer only) 1 hour

   Free public beach 5 min from Lincoln Park Zoo. Cruise-ship-shaped Beach House (locker rentals + restrooms). Volleyball nets, kayak rental $25/hr, paddleboard $30/hr. Lake Michigan water hits 21°C in August.

   Cost: Free (rentals $25-30/hr) TIP: Summer only (Jun-Sep). Off-season the path is still a beautiful sunset walk. Castaways Bar atop the Beach House for the $12-15 frozen cocktail with skyline view.
9. 16:30 Divvy bike ride along Lakefront Trail 1 hour

   Divvy bike-share $4 single ride + $0.20/min, or $15 day pass unlimited 3-hour rides. Lakefront Trail is 29 km of paved path from Bryn Mawr (north) to 71st St (south). Lincoln Park → Navy Pier → Museum Campus stretch is the iconic 8 km ride.

   Cost: $4-15 TIP: Download Divvy app — link credit card before arrival. Avoid rush hour (8am, 5pm) on shared paths. Helmets not included (bring your own or skip).
10. 16:45 Old Town walk + Wells Street historic district 30 min

    Pre-Second City wander through Old Town — Chicago's oldest residential neighborhood, brick row houses surviving the 1871 Fire. Twin Anchors Restaurant (since 1932, ribs $25-35, Sinatra's favorite booth still labeled). Free walking 30 min.

    Cost: Free TIP: Twin Anchors is one block from Second City — natural pre-show dinner. Reservations recommended for the heritage booth dining.
11. 17:00 Second City comedy show (1959, Tina Fey + Stephen Colbert alumni) 2 hours

    Iconic improv theatre at 1616 N Wells in Old Town — launched Tina Fey, Stephen Colbert, Steve Carell, Bill Murray, John Belushi. Mainstage show 80 min + free improv set after. $40-60 tickets.

    Cost: $40-60 TIP: Book 1-2 weeks ahead for weekends. UP Comedy Club (smaller venue same building) is cheaper $25-35. Arrive 30 min early — bar serves cocktails inside the theatre.
12. 19:30 Final dinner — Alinea (3-Michelin, book 6+ weeks) OR Andy's Jazz Club (heritage jazz) 3 hours

    Alinea $400-600 for the 20-course tasting (booking required 6+ weeks ahead). Andy's $15-35 cover + dinner for a heritage jazz finale.

    Cost: $15-600 TIP: Alinea is once-in-a-lifetime; Andy's is the easier Chicago-flavor finale.
13. 23:00 Optional late-night — Kingston Mines (3 bands nightly until 4am, Lincoln Park) 1-2 hours

    2548 N Halsted — Chicago's #1 blues club open until 4am. Two stages running simultaneously, no break between bands. $15-25 cover. Eric Clapton + Mick Jagger dropped in over the years.

    Cost: $15-25 TIP: 21+ only with ID. Cash + card. Weekends booked solid; weekdays walk-in. Pair with B.L.U.E.S. across the street ($10 cover) for cross-pollinating blues marathon.
14. 20:30 Departure — ORD via Blue Line ($5, 45 min) OR Uber ($35-50, 30-45 min) Transit

    Blue Line direct from downtown to ORD. Allow 3 hours pre-flight for international.

    Cost: $5-50 TIP: Blue Line is reliable + cheap. Uber faster if no traffic but rush hour can be slow.

Meal Recommendations

Activities

1. 08:30 Shedd Aquarium (open 9am) early entry 2 hours

   Largest indoor aquarium in the Western Hemisphere when it opened in 1930. 32,000 animals, beluga whales, dolphins, otters. Carribean Reef tank (319,000 liters) is the headliner. $40 standard, $50 with all-access (4D + sharks + dolphin show).

   Cost: $40-50 TIP: Open 9am — arrive 8:45 to be first in. Combine with Field via Museum Campus Pass $80. Tuesday after 4pm is Illinois resident free day (not for tourists).
2. 09:00 Field Museum of Natural History 3 hours

   World's largest T-Rex 'Sue' + 28m Maximo titanosaur + Egyptian mummies. On Museum Campus on the lakefront.

   Cost: $30 TIP: Museum Campus Pass $80 bundles Field + Shedd + Adler. Best morning before crowds.
3. 11:30 Adler Planetarium (Museum Campus, 3rd of the trio) 1.5 hours

   First planetarium in the Western Hemisphere (1930). Sky shows in Grainger Sphere + Definiti Theater. Best skyline-of-Chicago view from the south lawn promontory (the iconic skyline-with-Adler-in-foreground postcard shot).

   Cost: $25 TIP: Skip the planetarium itself if not space-curious — but the lawn outside is essential for skyline photos. Bring a tripod for night shots.
4. 13:00 Soldier Field exterior + 12th Street Beach 30-45 min

   Historic Soldier Field (1924, home of Chicago Bears NFL) — Greek-Revival colonnade exterior is free to view. Adjacent 12th Street Beach is a quieter alternative to North Avenue Beach with the same lake water + Adler Planetarium views.

   Cost: Free TIP: Bears game tickets $80-300 if in season (Sep-Jan). Otherwise just the architecture + beach photo stop.
5. 13:30 Lunch — Museum Campus café OR Eli's Cheesecake (downtown) 1 hour

   Field Museum café for convenience OR Uber 10 min to Eli's Cheesecake downtown café for the Chicago dessert institution.

   Cost: $15-30 TIP: Eli's downtown café is the more interesting choice — sampler plate of 5 cheesecakes.
6. 14:00 Museum of Science and Industry (MSI, Hyde Park) 3 hours

   Largest science museum in the Western Hemisphere. U-505 German U-boat (only WWII U-boat captured + brought to America), coal mine, Henry Crown Space Center. 30 min south from downtown.

   Cost: $25 TIP: Best for families with kids 8+. Metra commuter rail from Millennium Station (30 min) is more interesting than Uber.
7. 17:30 Hyde Park walk — University of Chicago + Obama Presidential Library site 1.5 hours

   University of Chicago campus (Gothic architecture from 1890s) + the Obama Presidential Library site (Jackson Park, opening 2026).

   Cost: Free TIP: Robie House (Frank Lloyd Wright, 1909) is on campus — tour $20 if open.
8. 19:30 Dinner — Valois Cafeteria (Obama's favorite) OR Hyde Park restaurant 1.5 hours

   Valois Cafeteria (53rd Street, since 1921 cash-only cafeteria — Obama's longtime favorite, served on his menu). Cheap + authentic Chicago experience.

   Cost: $10-20 TIP: Cash only. Cafeteria style — point at what you want. Obama mentioned in interviews multiple times.
9. 21:00 Promontory Point sunset walk OR Metra back downtown 45 min

   Promontory Point (55th Street + lakefront) is the Hyde Park sunset spot — limestone seawall with downtown skyline framed across the lake 12km north. Free, locals-only feel.

   Cost: Free TIP: Skip if it's freezing — Metra 55th-56th-57th station back downtown takes 25 min. Bring a layer even in July; lake breeze drops 5-7°C after dark.

Meal Recommendations

Activities

1. 08:30 Garfield Park Conservatory (free, 1908) 1 hour

   One of the largest conservatories in the US — 2 acres of indoor gardens (palms, ferns, desert house, aroid house with banana trees + jade vine). Free entry, donations welcome. Green Line 'Conservatory-Central Park Drive' station is at the door.

   Cost: Free TIP: Free guided tours Sat-Sun 1pm. Weekday mornings have almost no visitors. Avoid Garfield Park neighborhood after dark — Conservatory itself is well-policed during open hours.
2. 10:00 Pilsen — 18th Street mural walk + Mexican neighborhood 2.5 hours

   Chicago's Mexican-American cultural heart since the 1950s. Murals along 18th Street + Cermak. National Museum of Mexican Art (free entry).

   Cost: Free (museum free) TIP: Best mural concentrations: 16th + 18th Streets. National Museum of Mexican Art ($10 donation) has best US Mexican-American art collection.
3. 12:30 Lunch — Carnitas Uruapan (Pilsen, since 1975) 1 hour

   Pilsen's most-respected carnitas — slow-roasted pork sold by the pound. Build your own tacos with their handmade tortillas. $8-15.

   Cost: $8-15 TIP: Cash + card. Sunday morning has lines out the door. Order pork by the half-pound + tortillas + salsa + lime.
4. 13:30 Thalia Hall + Dusek's Board & Beer (Pilsen, 1892) 1 hour

   Restored 1892 opera house at 1807 S Allport — now a music venue + restaurant. Dusek's serves Bohemian-Czech revival cuisine $20-35 (Czech goulash, schnitzel, beer). Heritage architecture; perfect post-mural sit-down.

   Cost: $20-35 (or skip) TIP: Skip if Carnitas Uruapan filled you up — otherwise the building alone is worth a coffee + a look at the upstairs venue.
5. 14:00 Wicker Park — Milwaukee Ave + The 606 trail 2 hours

   Chicago's hipster + indie heart. Milwaukee Ave for indie boutiques + record stores + craft beer. The 606 (elevated rail-to-trail) connects neighborhoods.

   Cost: Free TIP: Blue Line 'Damen' station is the heart. Big Star tacos + margaritas if hungry.
6. 15:30 Reckless Records + Myopic Books (Wicker Park indie pause) 45 min

   Reckless Records (1532 N Milwaukee) is the legendary 1988 record shop — vinyl, CDs, used. Myopic Books next door (Chicago's oldest used bookstore since 1991) has 80,000+ titles + Sunday poetry readings. Both free to browse.

   Cost: Free browsing TIP: Reckless has live in-store performances most Saturdays 4-5pm. Cash-only tipping for visiting musicians.
7. 16:30 Final coffee — Sawada or Big Shoulders (West Loop indie) 1 hour

   Sawada Coffee (West Loop, signature charcoal latte) or Big Shoulders Coffee (multiple locations, indie roaster). 4th-wave coffee culture.

   Cost: $5-10 TIP: Sawada's charcoal latte is the Instagram order. Big Shoulders has the better espresso program.
8. 17:00 Time Out Market (Fulton Market food hall, since 2019) 1 hour

   Curated food hall at 916 W Fulton — 18 vendors picked by Time Out editors. Bonci pinsa pizza, Aba Mediterranean, Daisy's Po-Boy. $15-30 grazing dinner before Green Mill.

   Cost: $15-30 TIP: Easier than committing to one Greek Town restaurant. Rooftop bar opens summer. Pink Line 'Ashland' or Green Line 'Morgan' station.
9. 17:30 Pre-show dinner — Crisp (Korean fried chicken, Lakeview) OR Tank Noodle (Vietnamese, Argyle) 1 hour

   Crisp at 2940 N Broadway for crunchy Korean fried chicken wings $13-18 — quick pre-Green Mill bite. Tank Noodle (4953 N Broadway, walking distance from Green Mill on Argyle 'Asia on Argyle' strip) for $10-15 pho.

   Cost: $10-18 TIP: Argyle is Chicago's Southeast Asian commercial strip — Vietnamese + Cambodian + Thai. Tank Noodle is cash-only + closes 8pm. Crisp takes card.
10. 18:00 Final dinner — Green Mill (since 1907 Al Capone speakeasy, jazz) OR Sunday Poetry Slam 3 hours

    Green Mill $15-25 cover + cocktails. Sundays feature the Uptown Poetry Slam (invented here 1986). No phones on dance floor; original art deco interior.

    Cost: $15-50 + dinner TIP: ID required (21+). Red Line to Lawrence + 5 min walk. Casual dress. Pre-show dinner at adjacent restaurants.
11. 21:00 Optional final stop — Hopleaf Bar (Andersonville, 2002, Belgian beer) 45 min nightcap

    5148 N Clark, walking distance from Green Mill. 200 beer list strong on Belgian + Trappist ales. Mussels-and-frites $20-26 + Wisconsin cheese plate. 21+ only, no children after 8pm.

    Cost: $10-26 TIP: Easy Red Line ride back south to downtown when done. Kitchen closes 11pm weekdays / midnight Fri-Sat.
12. 22:00 Departure — ORD via Blue Line OR Uber Transit

    Final wrap. Blue Line $5 / Uber $35-50 from Uptown.

    Cost: $5-50 TIP: Allow 3 hours pre-flight international.

Meal Recommendations

Activities

1. 07:00 Option A — Detroit (3.5h drive / 1h flight) — Motown + Henry Ford Museum overnight Full day + overnight

   Drive 3.5h east on I-94. Motown Museum (Hitsville USA), Henry Ford Museum (Dearborn — best US car museum, Ford Rouge factory tour). 1 night Detroit.

   Cost: $200-400 car + hotel TIP: Henry Ford Museum is essential for car/industrial-history fans. Motown Museum is small but iconic.
2. 08:00 Option B — Indiana Dunes National Park (1h drive) — Lake Michigan beaches + dunes Full day

   1h drive east on I-90. 12,000-acre national park with sand dunes + Lake Michigan beaches. Mount Baldy (38m moving dune) hike + 3-mile beach.

   Cost: $25 park + gas TIP: Best summer (Jun-Sep) for beach. Spring/fall for hiking without crowds.
3. 11:00 Option B — South Shore Line train (no car needed for Indiana Dunes) Half day

   South Shore Line commuter rail from Millennium Station to 'Dune Park' station ($16 round-trip, 90 min one-way). Walk 15 min to West Beach trailhead. The car-free Indiana Dunes alternative.

   Cost: $16 round-trip TIP: Trains run hourly. Returns until 9pm. Pack lunch + water — limited food at the park itself.
4. 10:00 Option C — Chicago → NYC (2.5h flight $100-200) — Times Square + Statue of Liberty Full day + overnight

   Fly to NYC for a 1-night extension. Hotel near Times Square. Statue of Liberty ferry + Empire State Building.

   Cost: $100-200 flight + $200-400 hotel TIP: NYC for first US visit is essential — pair Chicago + NYC = complete Midwest + East coverage.
5. 09:00 Option D — Milwaukee Amtrak day trip (90 min, $25 one-way) Full day

   Hiawatha service Chicago Union Station → Milwaukee 7x daily. Harley-Davidson Museum ($24), Milwaukee Public Market lunch, Lakefront Brewery tour ($12 with samples), Pabst Mansion ($15). Last train back 10pm.

   Cost: $50 train + $60-80 attractions TIP: Easiest Day 6 option — no rental car, no overnight hotel. Pick this if Detroit feels too far and Indiana Dunes too low-effort.
6. 19:00 Return to Chicago — final downtown drinks before Day 7 wrap 1.5 hours

   Back from Day 6 extension. Cocktail at LH Rooftop (LondonHouse Hotel) or Sip-and-Stay at Cindy's. $14-22 cocktails with skyline views. Both walk-in.

   Cost: $14-22 TIP: Cindy's Rooftop walk-in is feasible weekday early evening. LH Rooftop has the better photo angle of the Wrigley Building + Trump Tower.
7. 20:00 Final dinner — Alinea (3-Michelin) OR Smyth (2-Michelin) 3 hours

   Alinea $400-600 (book 6+ weeks). Smyth $300-400 (book 4-6 weeks). Pre-departure splurge.

   Cost: $300-600 TIP: Michelin requires advance booking.

Meal Recommendations

Activities

1. 09:00 Final breakfast — Wildberry Pancakes (Loop, since 2007) 1 hour

   130 E Randolph St — local institution for stuffed pancakes (Crunchy French Toast Berry Short Stack, Cheery Cherry Berry). 30-50 min wait Sat/Sun; 10-15 min weekdays. $15-25 per person.

   Cost: $15-25 TIP: Walk-in only (no reservations). Arrive at 7:30am to skip the line. Cash + card.
2. 10:00 Final Mag Mile + Garrett Popcorn last shopping 3 hours

   Last walk on Michigan Avenue + final Garrett tin for souvenirs. Visit anything missed on Day 1.

   Cost: Shopping TIP: Garrett tin holds the popcorn fresh for 2-3 weeks; perfect gift home.
3. 12:00 Maxwell Street Market (Sunday only, 800 S Desplaines) 1.5 hours

   Historic Sunday market since 1912 — moved location but tradition preserved. 200+ vendors, Mexican street food (huaraches, tacos al pastor, tamales $4-8), vintage clothes + records. Best Sunday brunch with cultural energy.

   Cost: $10-25 TIP: Sunday 7am-3pm only. CTA Blue Line 'UIC-Halsted' is the closest stop. Skip if not Sunday — use this slot for Cindy's Rooftop.
4. 13:00 Final lunch — Lou Malnati's last deep dish OR Cindy's Rooftop sunset 1.5 hours

   Lou Malnati's $20-30 for one more deep dish (single-slice option). Cindy's Rooftop $35-80 for the final Bean-view cocktail.

   Cost: $20-80 TIP: Last chance for both Chicago icons.
5. 14:30 Buy ship-home Lou Malnati's deep dish (Tastes of Chicago) 15 min order

   Lou Malnati's ships frozen deep dish anywhere in continental US via tastesofchicago.com — order at the airport hotel or your phone. 4-pack $80 + shipping. Souvenir that actually gets used.

   Cost: $80-120 shipped TIP: Skip if international — they only ship US continental. Garrett Popcorn tin (carries on a plane) is the international-friendly alternative.
6. 14:00 Final Bean photo + Pritzker Pavilion goodbye 30 min

   Last 30 min at Millennium Park before departure. Final Bean reflection photo, walk through Lurie Garden (free 2.5-acre native-prairie garden behind Pritzker), Crown Fountain video-face spitting if it's summer.

   Cost: Free TIP: Storage lockers in Millennium Park underground garage hold luggage $5-10/day if your hotel checkout is morning + flight is evening.
7. 15:00 Departure — ORD via Blue Line OR Uber Transit

   Allow 3 hours pre-flight for international.

   Cost: $5-50 TIP: Blue Line $5 / Uber $35-50.

Meal Recommendations